Chapter 14 Su09SC - Organic Chemistry 5th Edition Paula Yurkanis Bruice Chapter 14 Aromaticity Reactions of Benzene Section 14.1 Benzene and

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Organic Chemistry 5 th Edition Paula Yurkanis Bruice Chapter 14 Aromaticity • Reactions of Benzene
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Benzene and Resonance In chapter 7, benzene and its resonance energy (36 kcal/mol) are introduced. Aromaticity is a form of resonance (delocalized electrons). Aromaticity can be precisely defined—we will use a set of criteria to identify aromatic compounds. Aromaticity has consequences for chemical reactivity. • Do you remember the criteria required for resonance? Section 14.1
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Benzene and Resonance (2) To have resonance, a molecule must have a series of uninterrupted p orbitals that are all in the same plane. Benzene is an example of a molecule with resonance. Every carbon is sp 2 -hybridized, so benzene is flat. Every carbon participates in a double bond, so every carbon has a p-orbital
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Criteria for Aromaticity Resonance: planar, uninterrupted pi system. Aromaticity: resonance criteria + cyclic odd number of pairs of pi electrons Section 14.2 Which compound fits these criteria?
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Aromatic? Are any of these aromatic? Section 14.3
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Cycloheptatrienyl bromide, or tropylium bromide, was first prepared in 1891. It is soluble in water but not in nonpolar solvents. Evidence Section 14.5
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Acidity of Alkanes vs. Cyclopentadiene Question: Why is the p K a of cyclopentadiene 15, while the p K a of ethane is 50?
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This note was uploaded on 05/31/2011 for the course CHEM 3341 taught by Professor Staff during the Spring '08 term at Georgia Southern University .

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Chapter 14 Su09SC - Organic Chemistry 5th Edition Paula Yurkanis Bruice Chapter 14 Aromaticity Reactions of Benzene Section 14.1 Benzene and

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